Sodium Iodide → HCID 403767, compound

HRID 970630Notes

Reaction equation

HRID 970630 reaction equation
[Na+].[I-:2].Br[CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[C:24]2[C:23]3[C:18](=[CH:19][C:20]([O:27][CH3:28])=[C:21]([O:25][CH3:26])[CH:22]=3)[C:17](=[O:29])[N:16]([CH3:30])[C:15]=2[C:14]2[CH:13]=[C:12]3[O:31][CH2:32][O:33][C:11]3=[CH:10][C:9]1=2>CC(C)=O>[I:2][CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[C:24]2[C:23]3[C:18](=[CH:19][C:20]([O:27][CH3:28])=[C:21]([O:25][CH3:26])[CH:22]=3)[C:17](=[O:29])[N:16]([CH3:30])[C:15]=2[C:14]2[CH:13]=[C:12]3[O:31][CH2:32][O:33][C:11]3=[CH:10][C:9]1=2

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 69508966HCID 69508966, compound

Product 1

HCID 403767HCID 403767, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

NaI (217 mg, 1.45 mmol) was added to a suspension of bromide 19 (70 mg, 0.15 mmol) in acetone (15 mL). The reaction mixture was heated at reflux for 12 h, after which the resulting orange precipitate was collected by vacuum filtration and purified by flash chromatography (silica gel, CHCl3) to provide 24 (73.0 mg, 95%) as an orange solid: mp 173-174.5° C.; IR (KBr) 2944, 1612, 1522, 1481, 1254, 1033 cm−1; 1H NMR (500 MHz, CDCl3) δ 7.88 (s, 1H), 7.43 (s, 1H), 7.40 (s, 1H), 7.36 (s, 1 H), 6.84 (t, J=7.22 Hz, 1H), 6.05 (s, 2H), 4.08 (s, 3H), 4.04 (s, 3H), 4.00 (s, 3H), 3.35 (t, J=6.69 Hz, 2H), 2.95 (q, J=7.32 Hz, 2H), 2.19 (m, 2H); ESIMS m/z (rel intensity) 532.1 (100, MH+). Anal. Calcd for C24H22INO5: C, 54.25; H, 4.17; N, 2.64. Found: C, 54.64; H, 4.25; N, 2.60.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 12 h
  3. filtrationafter which the resulting orange precipitate was collected by vacuum filtration
  4. custompurified by flash chromatography (silica gel, CHCl3)

Sources & evidence

ORD record
ord-4780b545813e4825b4287633938a0a56
Source dataset
uspto-grants-2007_12
Patent number
US07312228B2

Reaction notes

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